I used to be a winamp kid. Winamp is nice, small, does what it's supposed to do. But iTunes is like a brand new car. Sure it drives just like your 1994 Volvo did but it does it better and oh so much more. Seriously get it now, try it out.
Update: Took less then 10 minutes before all 6 computers in our apartment were playing music off each others playlists. =)